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Synthesis 2014; 46(06): 687-721
DOI: 10.1055/s-0033-1338594
review
© Georg Thieme Verlag Stuttgart · New York

Sequential Addition and Cyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

Giorgio Abbiati
a   Dipartimento di Scienze Farmaceutiche – Sezione di Chimica Generale e Organica ‘A. Marchesini’, Università degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy
,
Antonio Arcadi*
b   Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell’Aquila, Via Vetoio, 67010 Coppito, L’Aquila, Italy   Fax: +39(0862)433033   Email: antonio.arcadi@univaq.it
,
Fabio Marinelli
b   Dipartimento di Scienze Fisiche e Chimiche, Università degli Studi dell’Aquila, Via Vetoio, 67010 Coppito, L’Aquila, Italy   Fax: +39(0862)433033   Email: antonio.arcadi@univaq.it
,
Elisabetta Rossi
a   Dipartimento di Scienze Farmaceutiche – Sezione di Chimica Generale e Organica ‘A. Marchesini’, Università degli Studi di Milano, via G. Venezian 21, 20133 Milano, Italy
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Further Information

Publication History

Received: 02 October 2013

Accepted after revision: 06 November 2013

Publication Date:
12 February 2014 (online)

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Abstract

This review examines sequential processes involving α,β-ynones and α,β-ynoates containing proximate nucleophiles as useful building blocks for the synthesis of heterocyclic derivatives through conjugate-addition-type, pericyclic and transition-metal-catalyzed transfer hydrogenation, hydroarylation, hydrovinylation, or hydroalkynylation reactions followed by heterocyclization.

1 Introduction

2 Conjugate Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

2.1 Conjugate Addition–Annulation Reactions of β-(2-Amino­aryl or Heteroaryl)-α,β-Ynones

2.2 Sequential Reactions of γ-Hydroxy-α,β-Acetylenic Esters with Nucleophilic Reagents

2.3 Sequential Electrophilic Addition–Annulation Processes of α,β-Ynones Containing Proximate Nucleophiles

3 Cycloaddition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

3.1 [2+2] and [4+2] Cycloaddition–Annulation Reactions

3.2 1,3-Dipolar Cycloaddition–Annulation Reactions

4 Transition-Metal-Catalyzed Addition–Heterocyclization Processes of α,β-Ynones and α,β-Ynoates Containing Proximate Nucleophiles

4.1 Palladium-Catalyzed Transfer Hydrogenation–Heterocyclization Processes

4.2 Palladium-Catalyzed Hydroarylation–Heterocyclization Processes

4.3 Rhodium-Catalyzed Hydroarylation–Heterocyclization Processes

4.4 Copper-Catalyzed Hydroarylation–Heterocyclization Processes

4.5 Transition-Metal-Catalyzed Hydrovinylation–Heterocyclization Processes

4.6 Transition-Metal-Catalyzed Hydroalkynylation–Heterocyclization Processes

5 Conclusion

Key words

aminoalkynones - hydroxyalkynoates - sequential reactions - annulation - heterocycles